YOU SAID:
Timmy cried and cried and cried and cried over the lost of his favorite little boy Billy.
INTO JAPANESE
彼は泣きに泣いた。
BACK INTO ENGLISH
He cried and cried.
INTO JAPANESE
彼は泣きに泣いた。
BACK INTO ENGLISH
He cried and cried.
That didn't even make that much sense in English.